Chapter 6 Part 4

Perhaps a little pain was exactly what she needed! Straining against her bindings with all of her remaining strength, Grayfia cried out in a mixture of ecstasy and agony, the fiery sensations on her limbs at war with the sensation of Issei's mouth and length. In the end though, the ropes snapped and Grayfia's hands and legs were abruptly free.

Before Issei could even react, the silver haired devil had struck. One hand curled into the back of his brown hair, dragging him up off of her breasts to her mouth where she stuck her tongue down his throat and kissed the hell out of him. The other hand slid down between their bodies as she spread her legs a bit further, reaching under his thrusting cock to grab at his nut sack, which she gently massaged. Grayfia knew this would work and work it did, sending Issei right over the edge as she muffled his pleasure filled groan with her lips.

He came inside of her for what felt like ages, leaving Grayfia feeling more bloated than Sirzechs ever had. Eventually though, Issei pulled back from her and Grayfia let him go, her wrists and ankles already beginning to heal as she laid back on the bed, panting as her massive naked lactating chest heaved up and down. She knew she was red faced, she knew she was flustered and disheveled and aroused… but Grayfia also knew she'd won. Any minute now Issei's cock would start to shrink and soften. The young man couldn't possibly be able to keep it completely hard through more than two consecutive orgasms.

Yet, as she stared down the slope of her body in triumph, that feeling of impending victory slowly faded away and said triumph fled from her eyes to be replaced by abject shock as Issei stayed at full mast. Surprised as she was, Grayfia didn't even try to resist when Ddraig appeared above her on the bed, grabbing hold of her wrists and pulling them up over her head. Issei grabbed her by the thighs and spread her legs wide, ready and able to push back into her for another go when he looked up and caught the look in her eyes, pausing briefly to grace her with a roguish grin.

"What? Did you think I would make a bet like that if I could only last a couple rounds Grayfia? Have you truly been serving someone that incapable of pleasuring you? You haven't even cum around my dick yet. How could I call myself a man if I exhausted myself before making sure you were also satisfied?"

Here Issei paused and gained a wicked twinkle in his eye as he smirked rather sadistically.

"Though, I have to say… I wasn't expecting you to break free solely to bring me pleasure. You really are a dutiful maid, aren't you? Once you're MY maid, I promise I will always treat you as you deserve."

Grayfia's eyes widened but before she could say anything in response to that, Issei was back inside of her and the majority of her attention was once more focused on trying to stifle the noises threatening to escape from her mouth. He was right though, even if she only realized it now after the fact. Hell, that made it worse, didn't it?

She had had a chance to attack the young man currently fucking her. She'd had the element of surprise and even in her weakened state; she could have dealt him a crippling blow. She had held his balls in her hand and rather than crush them, she'd PLAYED WITH THEM! What had she been thinking? Upon further self-reflection, Grayfia understood that she hadn't been thinking at all and that was the insidious problem with all of this.

The silver haired devil couldn't be sure whether it was the young man's seductive power or her own personality, but she had allowed herself to get caught up in his flow, in his game. Grayfia had focused so totally on the bet she'd made with him that she'd forgotten he was in fact holding her against her will first and foremost, and any chance she could take to escape and report what was happening here to her King was one she should have jumped at.

Instead, she'd been convinced that she could win their little wager. She'd even had preliminary plans for what she would do to the young man once he was forced to free her, and not all of them had involved death. None of those plans would be feasible now though, not after she'd found out her assumptions regarding Issei's stamina were completely wrong.

Was he at the end of his rope now though at least? P-Perhaps she could just make it through one more release and he would finally go soft. She just had to fight back a little longer, right? As if reading her mind, Issei took that moment to lean over her, grabbing a fistful of her silver hair and pulling her head up so that their foreheads were nearly touching as he continued to plow her on his bed. Their eyes met as he spoke with a wide, wicked grin on his face.

"I can see what you're thinking at this point Grayfia. That emotionless mask of yours has more cracks than I can count by now. You're wondering just how many more times I can cum before I'm spent. You're wondering how much longer you have to last to have a chance at winning our little bet. Allow me to let you in on a little secret. My harem is my hoard. And as Ddraig's successor, my hoard is my power, my strength… and my stamina."

Grayfia stared up at the young man as he gloated, not quite understanding what he was saying. Or perhaps she just really didn't want to acknowledge it. Seeing her blank look, Issei grinned and clarified.

"To be clear, I don't sleep anymore, because my nights are spent satisfying my lovely ladies, one after another. So, all you have to do is last as long as all of them collectively. Now… are you ready for round three?"

A whimper left the silver haired devil's throat that she couldn't quite stop, as Issei reared back and then thrust into her harder than before, setting a new incredibly fast pace for this 'round'. Something inside of the stoic, strong, proud woman was breaking, bit by bit, piece by piece. She couldn't do it anymore; she couldn't hold back her orgasm indefinitely.

With her lactating tits jiggling back and forth from the force of his thrusts, Grayfia cried out and came on the spot, climaxing around Issei's pistoning dick and finally covering it in her pussy juices. Issei let out a startled laugh as her capitulation began, both of them knowing this was the start of the end for her. He never slowed down though, not even once as he fucked her cunt as hard as he could.

Grayfia moaned until something moved to cover her face, and then her cries and whines and moans were buried beneath dragon quim as Issei directed Ddraig to force the silver haired maid to eat her out. Ddraig's knees pinned Grayfia's wrists down to the bed even as she rode the beautiful devil's face, but there really wasn't a need to hold her down anymore. The fight was going out of her, slowly but surely. With one orgasm came more as the flood gates opened up. Grayfia reached climax after climax at the end of Issei's shaft and as her tongue laced up into Ddraig's insistent grinding mound, she wasn't sure she really wanted to resist anymore.

It would be easier, to just submit in the end…

-x-X-x-

Hours later, the Strongest Queen had done just that. The silver eyed beauty was broken, currently on her hands and knees with Issei's cock buried in her cunt as she bounced her hips back against it. The young man wasn't even thrusting into her anymore, simply leaning back on one hand while the other groped her fat jiggling ass. Grayfia was fucking herself on his shaft all on her own, while at the same time leaning forward to eat out Ddraig's sopping wet pussy, the dragon girl's clawed hand gripping her hair tightly.

Her large breasts shook back and forth under her, still lactating all over the bed. If Issei cared about the mess at all, he didn't say anything though and Grayfia was long past the point where she felt embarrassment about such things. After all, at this point her French maid uniform was disheveled and torn and streaked with cum. More than half of her beautiful body was visible by now, her creamy skin made all the creamier by the sticky white seed drying on it from Issei's numerous releases.

He'd cum on her and in her repeatedly and Grayfia had felt vindicated in giving up, as even now with her doing all the work, he was still rock hard, still at full master. Of course, technically she hadn't lost the bet yet. She'd never begged Issei for more, because she hadn't had to. He'd given it to her, over and over and over again, through orgasm after orgasm. He'd never stopped fucking her and Grayfia knew that even if she could go home after this, she wouldn't ever be the same again. Issei had unlocked something deep inside of her. The prim and proper maid was gone. In her place was a slut, excited and eager to begin working for her new Master.

Of course, that didn't stop her from freaking out when Issei abruptly got back into things, pulling out of her cunt while at the same time spreading her big bubble butt wide open. Grayfia's eyes widened just as much as she suddenly felt his tip against her tight untouched sphincter. She pulled back from Ddraig's cunt and whipped her head around to stare at Issei in fear.

"W-what are you doing?! That's the wrong hole!"

Issei grinned at her, teasing her contracting anus with his massive girthy tip, sliding his cockhead back and forth between her ass cheeks.

"It occurs to me that you haven't begged me yet Grayfia. I can't have a maid that thinks she's better than me now. I'm guessing you never let your former Master fuck this hole. I suppose that means it's up to me to train it properly."

Grayfia shook her head back and forth as best she could with a disgruntled Ddraig still holding her by her hair and clearly wanting her back between the dragon girl's legs.

"N-No! W-wait! Please Issei, please! M-Master, fuck my cunt! Don't touch my ass, I'm begging you! Please pump your warm hot seed into my womb again, plow my pussy senseless with your massive member! J-Just not there! It'll never fit!"

A pause as Issei smiles at Grayfia's words. The silver haired devil knows she's lost the wager and the last small bit of resistance within her dies as the crass, sexual words leave her mouth, but Grayfia is too focused on protecting her butt to care, staring at Issei in honest fear as he considers her briefly.

"Welcome to my service slut. Unfortunately, I can't allow one of my pets to continue on so ignorant of what pleasure can be found from your third hole. Not to worry Grayfia… you're going to enjoy this."